2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-[3-(4-fluorophenyl)-propyl]-n-methoxy-acetamide → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(4-fluorophenyl)-propyl]-methoxy-amide

HRID 2214725Notes

Reaction equation

HRID 2214725 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:23])O1.[CH2:25]=O.[NH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CO>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH2:13][N:10]([O:11][CH3:12])[C:8]([C:7]2[CH2:25][N:27]([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:4](=[O:23])[C:5]=2[OH:6])=[O:9])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 738555872-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-[3-(4-fluorophenyl)-propyl]-n-methoxy-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046674-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(4-fluorophenyl)-propyl]-methoxy-amideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methoxy-acetamide (0.560 g, 1.66 mmol) with the paraformaldehyde-N-(2-aminoethyl)morpholine adduct in methanol using a procedure similar to the one described in the preparation of compound 13 gave 0.446 g (63% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (DMSO-d6) δ (ppm); 1.84 (2H, m, CH2), 2.40 (4H, broad, 2×NCH2), 2.46 (2H, t, J=6.5 Hz, CH2), 2.56 (2H, t, J=8.1 Hz, CH2), 3.46 (2H, t, J=6.5 Hz, NCH2), 3.52 (3H, s, OCH3), 3.55 (4H, broad, 2×OCH2), 3.67 (2H, t, J=7.1 Hz, NCH2), 3.95 (2H, s, NCH2), 7.09 (2H, m, aromatics), 7.23 (2H, m, aromatics). HRMS (FAB+) calculated for C21H29FN3O5: [M+H]+: 422.209125. found: 422.208679.

Sources & evidence

ORD record
ord-6138978201c8424a92eb494ad076eff8
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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